Juncusol

Juncusol is a 9,10-dihydrophrenathrene found in Juncus species such as J. acutus,[1] J. effusus[2][3] or J. roemerianus.[4][5]

Juncusol
Names
Preferred IUPAC name
5-Ethenyl-1,6-dimethyl-9,10-dihydrophenanthrene-2,7-diol
Other names
1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H18O2/c1-4-13-10(2)17(20)9-12-5-6-14-11(3)16(19)8-7-15(14)18(12)13/h4,7-9,19-20H,1,5-6H2,2-3H3
    Key: XNVMKPYDOHZJLR-UHFFFAOYSA-N
  • CC1=C(C=CC2=C1CCC3=CC(=C(C(=C32)C=C)C)O)O
Properties
C18H18O2
Molar mass 266.340 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It can also be synthesized.[6][7][8]

This compound shows antimicrobial activity against Bacillus subtilis and Staphylococcus aureus.[4] It also has a toxic effect on estuarine fish and shrimp.[9]

References
  1. Behery, Fathi Abdelmohsen Abdelhalim; Naeem, Zain Elabdin Metwally; Maatooq, Galal Taha; Amer, Mohamed Mahmoud Abdelfattah; Wen, Zhi-Hong; Sheu, Jyh-Horng; Ahmed, Atallah Fouad (2007). "Phenanthrenoids from Juncus acutus L., New Natural Lipopolysaccharide-Inducible Nitric Oxide Synthase Inhibitors". Chemical & Pharmaceutical Bulletin. 55 (8): 1264. doi:10.1248/cpb.55.1264.
  2. Bhattacharyya (1980). "Structure of effusol: A new phenolic constituent from Juncus effusus". Experientia. 36: 27–28. doi:10.1007/bf02003949. S2CID 41731083.
  3. Shima (1991). "Phenanthrene derivatives from the medullae of Juncus effusus". Phytochemistry. 30 (9): 3149–3151. doi:10.1016/s0031-9422(00)98276-1.
  4. Chapatwala, Kirit D.; de la Cruz, Armando A.; Miles, D.Howard (1981). "Antimicrobial activity of juncusol, a novel 9-10-dihydrophenanthrene from the marsh plant". Life Sciences. 29 (19): 1997–2001. doi:10.1016/0024-3205(81)90609-3. PMID 6796796.
  5. Miles, D. H.; Bhattacharyya, J; Mody, N. V.; Atwood, J. L.; Black, S; Hedin, P. A. (1977). "The structure of juncusol. A novel cytotoxic dihydrophenanthrene from the Estuarine marsh plant Juncus roemerianus". Journal of the American Chemical Society. 99 (2): 618–20. doi:10.1021/ja00444a056. PMID 830696.
  6. McDonald, Edward; Martin, Roger T. (1978). "Total synthesis of juncusol". Tetrahedron Letters. 19 (47): 4723. doi:10.1016/S0040-4039(01)85715-4.
  7. Boger, Dale L.; Mullican, Michael D. (1984). "Regiospecific total synthesis of juncusol". The Journal of Organic Chemistry. 49 (21): 4045. doi:10.1021/jo00195a034.
  8. Jacobi, Peter A.; Zheng, Wanjun (1991). "A novel synthesis of juncusol". Tetrahedron Letters. 32 (10): 1279. doi:10.1016/S0040-4039(00)79645-6.
  9. de la Cruz, A. A.; Miles, D. H.; Chapatwala, K. D. (1982). "Toxic effects of juncusol, a marsh plant phenolic extract, on estuarine fish and shrimp". Life Sciences. 30 (21): 1805–10. doi:10.1016/0024-3205(82)90317-4. PMID 7098770.


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